Growing up in an Italian-American family, I have heard many stories about Italy’s beautiful sights, delicious food, and my mother's childhood experiences of spending her summers traveling throughout Europe with her sisters and brother. Our Italian culture is embedded into the foundation of my family, and I wanted to visit Northern Italy where my Grandpa's family originates from. The next time I visit Italy, I hope to visit the town of Montemurro in Southern Italy, where my Grandma's family is from.
A few months back, I booked a $15 flight to Milan with Delta miles and had no idea what to expect! I had been to Italy 10 years prior but wanted a more authentic experience, as opposed to guided tours. I was motivated to put together an itinerary that would be attractive enough to convince one of my girlfriends to join me!
I did a little bit of research, but not enough to avoid some of the common mistakes I made! For those interested in booking a similar itinerary, I will give you the day-by-day positives and negatives of my trip.
Day 1: Travel Day
Flight: DCA to JFK to Milan-Malpensa
Traveling can be exhausting, especially if you have long layovers or purchase economy class with less legroom than a smart car. If you can sleep on planes, I suggest taking a 9pm, 10pm, or 11pm redeye flight out of the US to Europe. You will arrive in Europe around 10am (depending on layovers) and have the whole day to explore.
(+) For those of you pressed for vacation days and PTO, taking an overnight flight is the best way to take advantage of your time off.
(-) Some hotels and Airbnb’s will not be accommodating to an early check in. You may have to entertain yourself for a few hours while carrying around your luggage.
Day 2: Explore Milan
Take the day to explore and see what Milano is about—eating delicious food, shopping the designer headquarters, and exploring some historical sites. Stay tuned for a detailed blog of where to eat, what to see, and what to do in Milan!
(+) We booked an AirBnb in a charming side of town, within walking distance to the sites we wanted to explore. If you’re interested, book here.
Day 3: Visit Lake Como or Switzerland by Train
Cadorna Station to Como
Take Ferrovie Nord from the Cadorna Train station to Lake Como. Make sure you get on the direct train to arrive within an hour! If you hop on the wrong train, it can take you up to 3 hours to reach your destination. Pro tip: Make sure you wear comfortable shoes on your trip to Lake Como. We underestimated the size of the lake, and you will want to walk around and explore.
(+) There are many destinations you can reach by an hour- or three-hour train from Milan. Other popular destinations include Venice, Rome, or Florence.
Day 4: Travel to Levanto
Book on Trainline: Milano Centrale to Levanto
We decided to stay in Levanto, which is not considered one of the 5 ‘cinque terres.’ It is a 5 minute train to Monterosso, which marks the 5th city.
(+) We booked a charming AirBnb with a fabulous host. She was so accommodating and lived a few floors down if we needed anything. She was our Italian grandma of the trip. Book here!
(-) Pack light, the entire town is an uphill battle with heavy luggage.
Day 5: Visit Cinque Terre
Cinque Terre 2 Day Pass
Buy a 2 Day Cinque Terre Pass to explore all 5 cities by train and foot trail. Each city is a 5-minute train ride from one another. The train is super easy to navigate and there is a train every hour running in each direction. Each city is charming and a little different, but our favorite was Vernazza.
(+) You can easily train to all 5 cities and hike up to the best views without being in athletic apparel.
(-) We visited in off season, but if you wait for June-August, you will see every town packed with visitors.
Day 6: Hike from Levanto to Monterosso
Apparently, the hikes between the 5 cities is less challenging than the hike from Levatno to Monteroesso. I do suggest the hike, but pack accordingly and know that you are up for a challenge. We underestimated the hike, thinking it was going to be an hour or two on a guided trail-- this was NOT the case. The trail is extremely difficult, dangerous, and takes roughly 4 hours long to complete. We were 3 hours into the hike, climbing on rock face, when we finally ran into another couple who told us we had another hour to go. Let’s just say we had quite the celebration when we finally reached Monterosso.
(+) The hike is rewarding and has some of the most breathtaking views.
(-) You need hiking boots, a liter of water, and a hiking backpack with essentials and snacks.
Day 7: Travel home
Levanto to Milano Centrale to Milan-Malapensa Hotel
On the last day of the trip, we traveled from Levanto back to Milan, and then headed straight to the airport hotel. I took an 8:45am flight out of Milan, and it was perfect. When traveling back to the US, it is better to leave Europe early in the morning. That way, if any leg of your flight gets delayed, you have a good chance of hopping on another flight once you reach the states.